TMSCFX2 (X = Cl, Br) as halofluorocarbene sources for the synthesis of halofluorocyclopropanes

Dingben Chen; Zili Fan; Ling Huang; Kaili Gao; Pan Xiao; Chuanfa Ni; Jinbo Hu

doi:10.1039/D0CC06004F

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TMSCFX₂ (X = Cl, Br) as halofluorocarbene sources for the synthesis of halofluorocyclopropanes†

Dingben Chen,

^ab Zili Fan,^a Ling Huang,^b Kaili Gao,^b Pan Xiao,^ac Chuanfa Ni

^a and Jinbo Hu

*^ac

Author affiliations

* Corresponding authors

^a Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, China
E-mail: jinbohu@sioc.ac.cn

^b School of Pharmaceutical and Materials Engineering, Taizhou University, Taizhou, Zhejiang, China

^c School of Physical Science and Technology, ShanghaiTech University, 100 Haike Road, Shanghai 201210, China

Abstract

TMSCFX₂ (X = Cl, Br; TMS = trimethylsilyl) have been developed as halofluorocarbene (CFX, X = Cl, Br) precursors for [2+1] cyclopropanation with alkenes. Structurally diverse halofluorocyclopropanes were obtained in good to excellent yields. It was found that the reactivity order of the three halofluorocarbene reagents (TMSCF₂Br, TMSCFCl₂, and TMSCFBr₂) in halofluorocyclopropanation with 1,1-diphenylethylene can be very different under different reaction conditions.

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Article information

DOI: https://doi.org/10.1039/D0CC06004F
Article type: Communication
Submitted: 05 Sep 2020
Accepted: 02 Dec 2020
First published: 08 Dec 2020

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Chem. Commun., 2021,57, 319-322

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TMSCFX₂ (X = Cl, Br) as halofluorocarbene sources for the synthesis of halofluorocyclopropanes

D. Chen, Z. Fan, L. Huang, K. Gao, P. Xiao, C. Ni and J. Hu, Chem. Commun., 2021, 57, 319 DOI: 10.1039/D0CC06004F

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